Howie Carr’s jump from WRKO-AM (680) to WTKK-FM (96.9) isn’t a done deal just yet. Carr’s new morning drive-time show is supposed to begin in October. But after the Herald reported this past Monday that Carr was poised to bolt WRKO, station spokesman George Regan released a statement hinting that WRKO might take legal steps aimed at keeping Carr from leaving — or, barring that, at making his exit as unpleasant as possible. “He is a tremendous asset to WRKO and Entercom [WRKO’s parent company] has every intention of retaining his services for many years to come,” said Regan. “Any report suggesting a change is incredibly premature.”

If the station has a case, it probably hinges on a clause in Carr’s contract that gives WRKO the right to match any competitor’s offer. But on Tuesday, Carr filed a pre-emptive lawsuit of his own, accusing WRKO of repeatedly declining to extend his contract, and arguing that any provisions aimed at keeping him from leaving for a competitor were legally unenforceable.

Whether the courts will agree remains to be seen. But even if they don’t, WRKO should think twice about mounting a fight. Carr’s relationship with WRKO seems to have been seriously strained even before this dust-up hit the headlines; now that things have reached this point, it’s hard to imagine the station and its marquee talent making peace.

One source with knowledge of the situation says that Carr — whose populist conservatism runs the gamut from witty erudition to juvenile mean-spiritedness — had accumulated a long list of grievances with WRKO. Among other things, he was concerned about the station’s declining ratings; he felt management wasn’t promoting or syndicating him effectively; and he bristled at being pre-empted for preseason Red Sox games, which WRKO began broadcasting this year in an awkward joint-broadcasting arrangement with WEEI-AM, Entercom’s Boston sports station. “Howie’s overall feeling is that it’s a poorly run operation,” this individual, who works in Boston radio, tells the Phoenix.

This casts a new light on the alleged feud between Carr and Tom Finneran — the ex–Massachusetts House Speaker who, after pleading guilty to perjury in a legislative-redistricting case, took over WRKO’s morning-drive-time slot earlier this year. In March, the Herald turned this purported beef into a cover story, reporting that Carr (who’s also a Herald columnist) was incensed after Finneran joked that he should be killed and stuffed in the trunk of Governor Deval Patrick’s car. At the time, I argued that the whole flap seemed to be a shameless publicity stunt. In retrospect, though, Carr’s stagy wrath may have obscured genuine frustration: a strong morning host would have helped Carr’s own ratings and market position by driving listeners to the station. But Finneran clearly wasn’t ready to fly solo — and hasn’t been given a reliable sidekick to help him along.

More significantly, Carr’s disenchantment and potentially imminent departure also raise questions about Entercom executive Jason Wolfe, who went from running WEEI’s programming to directing programming for both WRKO and WEEI in early 2006 and has been considered something of a golden boy in local radio circles. Given WEEI’s continued success, the underwhelming performance of WRKO under Wolfe’s watch is especially striking. Former hosts Scott Allen Miller and John DePetro are gone. Finneran is struggling in the morning drive-time slot, both in terms of ratings and in terms of establishing a compelling on-air persona. It’s still not clear how splitting the Red Sox between WEEI and WRKO helps either station. And now Carr — the station’s name-brand talent — is poised to bolt to its major competitor. (Wolfe and Julie Kahn, Entercom New England’s vice-president and market manager, did not return calls from the Phoenix.)

Strange bedfellows Wait, lemme get this straight: Was that Howie Carr — who's known for accompanying on-air references to homosexuality with a crude audio approximation of gay sex — happily schmoozing with guest Randy Price this past week?

The importance of being Ernie Media feuds don’t come any nastier than the metastasizing spat between Boston Herald columnist Howie Carr and one “Ernie Boch III,” the pseudonymous blogger at the liberal Web site Blue Mass. Group. (Note: the blogger is no relation to the car dealer.)

Murphy’s big tent In the past few years, Murphy has recast himself to reflect the changing city.

Fourth-estate follies, 2009 edition Between the rise of the Web, the ADD-addling of America, the fragmentation of any national political consensus, and the devastated economy, working in the press can feel a bit like manning the Titanic — and this year, the entire industry seemed to teeter on the edge of oblivion.

WPRO swaps two big personalities Talk-radio listeners could be forgiven for wondering if WPRO sprung a bit too far forward this week when Buddy Cianci's show begun airing at 2 pm instead of the usual 10 am.

Brass balls and cold steel John “Red” Shea’s close-cut hair — the hair that gave him that standard-issue Irish nickname — isn’t quite as fiery as it was when he was a young fighter coming up hard from G Street in South Boston.

Goal rush! Get two journalists in a room these days, and before the conversation is five minutes old they'll probably be kvetching about the grim state of the news business. Unless, that is, they happen to be sports journalists, in which case the conversation will likely focus on how absurdly bright the future looks. Especially here in Boston.

Where is the hate? Once upon a time, no one whipped up conservative rage like Ted Kennedy.

Republican radio If you’re a political liberal — or just someone who has a sense of fair play — listening to two straight days of talk on WRKO-AM isn’t easy.

BULLY FOR BU! | March 12, 2010 After six years at the Phoenix , I recently got my first pre-emptive libel threat. It came, most unexpectedly, from an investigative reporter. And beyond the fact that this struck me as a blatant attempt at intimidation, it demonstrated how tricky journalism's new, collaboration-driven future could be.

STOP THE QUINN-SANITY! | March 03, 2010 The year is still young, but when the time comes to look back at 2010's media lowlights, the embarrassing demise of Sally Quinn's Washington Post column, "The Party," will almost certainly rank near the top of the list.

RIGHT CLICK | February 19, 2010 Back in February 2007, a few months after a political neophyte named Deval Patrick cruised to victory in the Massachusetts governor's race with help from a political blog named Blue Mass Group (BMG) — which whipped up pro-Patrick sentiment while aggressively rebutting the governor-to-be's critics — I sized up a recent conservative entry in the local blogosphere.

RANSOM NOTES | February 12, 2010 While reporting from Afghanistan two years ago, David Rohde became, for the second time in his career, an unwilling participant rather than an observer. On October 29, 1995, Rohde had been arrested by Bosnian Serbs. And then in November 2008, Rohde and two Afghan colleagues were en route to an interview with a Taliban commander when they were kidnapped.

POOR RECEPTION | February 08, 2010 The right loves to rant against the "liberal-media elite," but there's one key media sector where the conservative id reigns supreme: talk radio.